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Seems easiest to just have it be this until we need more people: A consolidate Stage Lead and a consolidated Talent Lead who manage the club between them as Pres and Vice Pres and Treasurer.
So, this could be split easily enough: Directors among President and Vice President, a Treasurer, Talent Lead (or Actor, Singer, and Musician Leads), Stage Lead (or Props and Techie Leads).

Club Leads

Leads are: assured/charismatic and can play the group well enough (whether inspiration/ego-stoking/bribery or playing egos against each other) to keep them organized and functioning. Fan of mischief, as long as it doesn't throw things too far, while still keeping things to the parts of the schedule that actually need doing; is comfortable with dark humor and irony. Dedicated and respected by those who stick around through the organized chaos. Not afraid to push boundaries, but with a realistic eye to their audience as to what they can get away with and willing to be pragmatic about implementing that.

The default Directors and managers for any production; they do delegate though (gotta train the others up somehow after all and/or to get a bit of a break).

I was going to have the Stage lead persona alongside the lead stuff above as the Club President I had for my NPC (before consolidating positions and such) and the Talent lead just be another person in Drama group. It was mostly just to fill positions.

Talent Lead

He is rediculously charming, but also dating a guy outside the club. They might flirt or play to egos, but they're dating another and are unlikely to betray them for shiggles (though breakups or just having an understanding between the two is possible I suppose). Panache in letting down boys/girls who are enticed.

Another Junior or Senior; experienced and has been working with the club over a year or two at least.

Normally leads tryouts and such (not just them & delegates on occasion); helps send to other branches if necessary. Has apprentices within Acting and Singers and Musicians.

Part of how the various dramatically inclined are kept from erupting too badly; actively balances them

Managing the Talent takes enough time and energy to require extra bribery and prevents them from BEING the talent they were; they otherwise would be an exemplary example of skills needed for actor/singer/musician and every once in a while get to show that off.

Rose is an actor under their capable hands. (Perhaps he will be groomed as an apprentice if he opens up?)

The thought occurs that the boy the lead is dating could be the boy Andrea got Rose to admit about? Or perhaps the lead (I thought it was meant to be outside the club though) or a friend/family relation to one of them? If things go on long enough and resolve, they might see requests to assist Rose in learning certain things, so might as well eventually give them a name and personality and a slight association to one of us or others may be good (or bad).

Stage Lead

She has long dark hair, a nice figure if she works at it slightly and dresses up, and is a Junior or Senior.

While Andrea enjoys seeing Rose dressed up, Pres is probably the one who initially organized the situation leading to him dressing up; enjoys watching the effects it has on both Rose and Andrea (and perhaps some of the others in the school). Andrea probably helped during and/or teased about it throughout and will quite happily cause such situations herself now, though.

Andrea consider her to be one of the few authority figures she actually respects even if she occasionally is a source for extra chaos or is less pragmatic.

Organizes the stagehands, how the props/costumes/effects will be used; manages the techies that deal with lights/audio/video and remote effects. Has apprentices for stage hands and techies both.

Most intimately deals with costs: stages/lights/AV/props/costumes/effects/etc require purchase or materials/crafting as well as maintenance

Andrea is (mostly) a stagehand with some techie training under their capable hands. (Perhaps she will be groomed as an apprentice or is starting to be so trained already?)

Others:

Relatively puritan school girl, thinks lewd things are lewd but is already blushing under drama club corruption; can play villainess roles surprisingly well and/or belt out songs if properly coached, but otherwise stays in choir singing and upright citizen roles? Has figured out connatations about Catholic-schoolgirls is less than always pure, but still more than a bit innocent despite drama club. May secretly have seen some guy-on-guy stuff and thinks Rose looks too adorable in costumes, but is too busy not noticing that about the various other boys as well to do more than quickly acknowledge it. Can also play a mean keyboard though she might suggest setting it to traditional piano instead of synth. Singing with the techie-guy is rather nice, but she tries to ignore impure thoughts about what he'd look like if she helped him see the sun a bit more and work out a bit (though same for some of the other boys too).

Fairly lean-muscled guy; totally just there to ogle girls and not learn to dance, except the part that helps his football and not because he likes dancing at all (may eventually figure out that dancing helps get him girls, but now it'd just be an excuse). Into sports and girls, and ever so gradually getting better at dealing with both; very little free time between drama club and sports though, and drama gets dropped fairly frequently (to his dismay). Actually fairly good at dancing, and can play Bravo types well enough though any singing is backup only; probably warned off gay-bashing, but still makes the occasional mistake especially when around his sports team. Could easily help with physical tasks, and normally does if around.

Strident devas, in black and blonde hair and striking figures (well, enough for high-school with the outfits and makeup they can manage). A bit of cat-fighting and such, and some quality acting/singing (and at least decent dancing), but dealing with them is something the Lead has to monitor more than for others. Whether they manage to blend in with the drama club or stay devas is a bit of a toss-up, but for now they're not apprentice worthy but that changing seems doable. Among the popular crowed, but on the lower tiers of such and probably worried because of such.

Smarmy guy who tries to be seen as with a heart of gold (or enough to be forgiven). Less smarmy than he seems, and perfectly capable when he relaxes trying so hard. Is starting to figure out he can just be nice and good at what he does and stay social, though the balance isn't right for him yet; he shows quite a bit of promise though and is getting it right more than wrong at this point. Probably dated both the divas, though it didn't work out; either no steady girlfriend yet or he just hasn't talked about it. Sophmore or Junion: he's been there a while and can be tasked to deal with things; good actor and dancer, passable singer, and can manage a few instruments well.

Nerdy guy who is shy; normally part of the tech crew, but is quality singer when pressed into service. Trying not to crush on the puritan school girl, but they duet very well (to some dismay by the divas). Worse than Rose at acting though, and better at refusing acting roles than him. Probably has been dressed up in female outfits as well, but not comfortable with them (possibly Puritan girl didn't mind so much though?). Could stand to get out in the sun, but not unfit. Not so good with instruments, but can mix digital music well enough; regularly does the AV portion of the techie side but is good with the lights/effects as well.

Girl who has a body she could show off, but prefers to stay behind the scenes; the lights are hers to control and woe betide those who would mess them up (she knows the best places to hang bodies from the rafters and how the electricity and cables flow). Can appreciate beefcake and Rose-in-a-dress, but starting to realize she prefer girls; dated the boy-twin of the stage-workers (friendly enough breakup), but is starting to take reciprocated interest in the girl-twin. Rather good at using the AV equipment as well, though normally singer-techie does that; she tolerates him taking her spot in her absence but few others (Andrea may play with patterns but doesn't mess up the equipment but generally she'd help in his spot while he mans the lights instead; the same can be done with others though lights-girl may complain). Manages effects with the other stage-hands and techies. Normally refuses to play instruments, but can manage woodwinds just fine if convinced (she showed up the divas once).

Reliable-ish guy who is rather good at difficult costumes; starting to play the pervert just a bit, but professional or normal outside him playing at it. Tetsuo probably makes a good example; barely knows what to do with a girl who goes along with it, but he'll learn to banter and flirt eventually and has been gaining confidence. Quite good at props as well, and probably a stage apprentice; sophomore. Can act small parts or backup sing, but mostly deals with costumes and props.

Twins (boy and girl) who are amazing at stage-work; they are not normally difficult to tell apart, though sometimes they are willing to pull pranks that make it difficult (even using props to help). Stage construction, backdrop painting, conduits for air/cable/etc are theirs to know. Lights-girl was dating the brother for a while, but that stopped early on (friendly breakup though); now lights-girl and the sister are starting to both figure out why they get along instead. Generally kind and nice, but also strong and capable and mechanically inclined; it takes awhile to anger them, but they could essentially build you into the floorboards or a small chest or force you wherever they wanted with little difficulty. They know what every sound the building makes is and why, mostly. Quite good at props as well, but normally only extras in acting and such; boy can do tech-work and play horns, girl can sing passably and play strings though. Juniors or Seniors, they've been around for awhile. Andrea basically treats them like older siblings and could perhaps be slightly distant cousins?

Rose is a natural for the younger parts given his age; having been found to look cute in dresses, that's for either gender. When he relaxes into the part, can play a justice-driven hero(/ine) well, though getting to that point regularly can be difficult; he is learning though and plenty of younger parts help with getting better. Getting him to play the villainess is amusing though. Coerced into wearing a dress for a quick part as a small scheme, but naturally took to it unlike the singing techie; hasn't protested nearly enough about later attempts and has somewhat accepted it's a requirement of some parts. Trained in some classical instruments, but is unlikely to volunteer unless pressed or he feels it is needed.

Andrea is more of an all-rounder with a side of improv: she can manage most tasks, if not incredibly well, and can make up gaps in an emergency. She is normally in charge of managing props alongside the other stagehands, but can jury-rig things if an immediate/temporary fix is needed in other areas and is reasonably capable as a techie; "inventive" with effects and lighting, but probably shouldn't be left unsupervised around such for too long unless it's important or a bit of deviation from the expected is fine. Passable as actor, singer, musician, or dancer, but not exceptional; she can improv well enough to help others settle in though or just wing something. Plays off suggestions she overly favors Rose but presumably those who bother to notice things know better than to accept that.